Tetrahydrofuran → N-(2-chloro-4-fluorophenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

HRID 84415

Reaktionsgleichung

Reaktionsgleichung von HRID 84415
[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:10](N(CC)CC)C.O1CCCC1.[S:22]1[C:26]2[C:27]3[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=3[O:29][CH2:30][CH2:31][C:25]=2[CH:24]=[C:23]1[C:36](Cl)=[O:37]>>[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[N:4]([CH3:10])[C:36]([C:23]1[S:22][C:26]2[C:27]3[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=3[O:29][CH2:30][CH2:31][C:25]=2[CH:24]=1)=[O:37]

Komponenten

5

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 75013Benzenamine, 2-chloro-4-fluoro-HCID 579001474,5-Dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonylchloride

Produkt 1

HCID 57900362N-(2-chloro-4-fluorophenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

Versuchsvorschrift

To a solution of 2-chloro-4-fluoroaniline (0.110 g, 0.755 mmol) and triethylamine (0.105 mL, 0.755 mmol) in tetrahydrofuran (1.5 mL, 18 mmol) was added portion wise as a solid 4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonyl chloride (0.100 g, 0.378 mmol). Reaction mix was stirred at room temperature with monitor for formation of desired product. The reaction was stirred overnight. The mixture containing the alkylated product was concentrated in vacuo to a solid residue, then taken into N,N-dimethylformamide (1.5 mL, 19 mmol) and treated with sodium hydride (0.0181 g, 0.755 mmol) followed by the addition of methyl iodide (0.0470 mL, 0.755 mmol). Reaction stirred at room temperature for about 1 hr with complete conversion to desired N-methyl derivative. After aqueous work up, the crude was taken into DMF at 100 mg/l mL and purified by preparative RP-HPLC to give 107. Yield=22% of theoretical. MS: (ESI+) 375

Aufarbeitung

  1. customReaction
  2. additionmix

Quellen und Nachweise

ORD-Eintrag
ord-04f201a650f945e997c39f16493c2296
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

Verknüpfte Notizen

Wird geladen…